Ammonium Chloride → N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide

HRID 493602

반응식

HRID 493602 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C([Li])(C)(C)C.C(C1C=CC(S([N:41]=[N+:42]=[N-:43])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>O1CCCC1>[N:41]([C:4]1[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[N+:42]=[N-:43]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 109151434-Dodecylbenzenesulfonyl azideHCID 22293237N-(5-Fluoropyridin-2-yl)pivalamideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 22293288N-(3-Azido-5-fluoropyridin-2-yl)-2,2-dimethylpropanamide수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a −78° C. solution of N-(5-fluoropyridin-2-yl)-2,2-dimethylpropanamide (1.34 g, 6.83 mmol) in tetrahydrofuran (25 mL) was added tert-butyllithium (1.31 mL of a 1.7 M solution, 20.5 mmol) drop wise. After 3 h at −78° C., 4-dodecylbenzenesulfonyl azide (3.60 g, 10.2 mmol) was added at the reaction was allowed to warm to room temperature. After 1 h, saturated aqueous NH4Cl was added, and the tetrahydrofuran was removed via rotary evaporator. Dichloromethane was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes, then 5%→42% EtOAc/hexanes) to give the title compound (0.275 g). MS 234.0 (M+1).

후처리

  1. waitAfter 1 h
  2. customthe tetrahydrofuran was removed via rotary evaporator
  3. additionDichloromethane was added
  4. customthe layers separated
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by two successive silica gel chromatographies (10%→80% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-221d8b8b440d4c45ba5e9ffec9428080
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534784B2

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